#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011322.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2011322
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  1164
_journal_page_last  1167
_publ_section_title
;
From \a-carbamoyl-\a-cyanooxiranes to 3-halogenopyruvamides;
3-(4-chlorophenyl)-2-cyano-2,3-epoxypropanamide,
3-bromo-2-cyano-2-hydroxy-3-(m-tolyl)propanamide,
3-bromo-2-oxo-3-(m-tolyl)propanamide and
3-chloro-2,2-dihydroxy-3-phenylpropanamide
;
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_[local]_cod_cif_authors_sg_H-M  'C 2/c'
loop_
_publ_author_name
  'Lah, Nina'
  'Leban, Ivan'
  "Majcen-Le Mar\'echal, Alenka"
  'Le Grel, Philippe'
  'Robert, Albert'
  'Sieler, Joachim'
  'Giester, Gerald'
_chemical_formula_moiety  'C10 H10 Br N O2'
_chemical_formula_sum  'C10 H10 Br N O2'
_chemical_formula_weight  256.10
_symmetry_cell_setting  'monoclinic'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  22.614(5)
_cell_length_b  10.257(2)
_cell_length_c  10.099(2)
_cell_angle_alpha  90.00
_cell_angle_beta  114.32(3)
_cell_angle_gamma  90.00
_cell_volume  2134.6(8)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.594
_diffrn_ambient_temperature  293(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  Br  .33339(2)  .18643(4)  .33990(4)  .0648(2) Uani d . 1 . . Br
  O2  .30305(12)  .4924(3)  .4623(3)  .0706(8) Uani d . 1 . . O
  O1  .42285(11)  .4607(3)  .3368(2)  .0521(7) Uani d . 1 . . O
  N1  .43410(14)  .5051(3)  .5646(3)  .0548(8) Uani d . 1 . . N
  H1  .4749  .5213  .5951  .055(11) Uiso calc R 1 . . H
  H2  .4154  .5109  .6232  .072(13) Uiso calc R 1 . . H
  C1  .40018(15)  .4713(3)  .4276(3)  .0422(8) Uani d . 1 . . C
  C2  .32834(16)  .4462(3)  .3879(3)  .0433(8) Uani d . 1 . . C
  C3  .29390(15)  .3588(4)  .2601(4)  .0432(8) Uani d . 1 . . C
  H3  .3065  .3832  .1815  .037(8) Uiso calc R 1 . . H
  C4  .22207(16)  .3498(4)  .2005(4)  .0458(9) Uani d . 1 . . C
  C5  .18556(18)  .3691(4)  .0542(4)  .0563(10) Uani d . 1 . . C
  H5  .2062  .3876  -.0066  .053(10) Uiso calc R 1 . . H
  C6  .1187(2)  .3614(5)  -.0030(5)  .0701(12) Uani d . 1 . . C
  H6  .0951  .3758  -.1019  .086(14) Uiso calc R 1 . . H
  C7  .0863(2)  .3332(4)  .0816(5)  .0705(13) Uani d . 1 . . C
  C8  .1225(2)  .3145(5)  .2288(6)  .0780(14) Uani d . 1 . . C
  H8  .1014  .2965  .2886  .098(16) Uiso calc R 1 . . H
  C9  .1894(2)  .3219(4)  .2885(5)  .0690(13) Uani d . 1 . . C
  H9  .2128  .3083  .3876  .080(14) Uiso calc R 1 . . H
  C11  .0134(2)  .3201(6)  .0186(8)  .103(2) Uani d . 1 . . C
  H11A  -.0040  .3333  -.0846  .11(2) Uiso calc R 1 . . H
  H11B  -.0042  .3842  .0616  .16(3) Uiso calc R 1 . . H
  H11C  .0020  .2345  .0388  .105(19) Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  Br  .0559(3)  .0615(3)  .0704(3)  .0063(2)  .0194(2)  -.0018(2)
  O2  .0413(15)  .107(2)  .0689(18)  -.0057(15)  .0278(13)  -.0322(16)
  O1  .0370(13)  .085(2)  .0362(12)  -.0090(12)  .0174(10)  -.0044(11)
  N1  .0329(17)  .095(3)  .0370(15)  -.0141(16)  .0149(13)  -.0121(15)
  C1  .0331(18)  .054(2)  .0375(18)  -.0009(15)  .0129(14)  .0007(14)
  C2  .0336(18)  .049(2)  .0448(18)  -.0003(16)  .0140(14)  .0004(15)
  C3  .0295(18)  .057(2)  .0427(19)  -.0011(15)  .0141(14)  .0027(15)
  C4  .0313(18)  .056(2)  .0463(19)  -.0050(16)  .0120(15)  -.0016(15)
  C5  .039(2)  .069(3)  .053(2)  -.0091(19)  .0119(17)  -.0049(18)
  C6  .046(2)  .083(3)  .060(3)  -.002(2)  .001(2)  -.003(2)
  C7  .036(2)  .066(3)  .099(3)  -.0085(19)  .017(2)  -.007(2)
  C8  .046(2)  .100(4)  .095(4)  -.014(2)  .037(3)  .006(3)
  C9  .045(2)  .100(4)  .061(3)  -.011(2)  .021(2)  .010(2)
  C11  .037(3)  .100(5)  .152(6)  -.009(3)  .019(3)  -.005(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  Br C3 . 1.995(4) yes
  O2 C2 . 1.212(4) yes
  O1 C1 . 1.225(4) yes
  N1 C1 . 1.322(4) yes
  N1 H1 .  .8600 ?
  N1 H2 .  .8600 ?
  C1 C2 . 1.526(5) yes
  C2 C3 . 1.500(5) yes
  C3 C4 . 1.485(5) yes
  C3 H3 .  .9800 ?
  C4 C5 . 1.379(5) yes
  C4 C9 . 1.399(5) yes
  C5 C6 . 1.381(6) yes
  C5 H5 .  .9300 ?
  C6 C7 . 1.366(6) yes
  C6 H6 .  .9300 ?
  C7 C8 . 1.384(7) yes
  C7 C11 . 1.510(6) yes
  C8 C9 . 1.380(6) yes
  C8 H8 .  .9300 ?
  C9 H9 .  .9300 ?
  C11 H11A .  .9600 ?
  C11 H11B .  .9600 ?
  C11 H11C .  .9600 ?
_cod_database_code 2011322